DE87973C - - Google Patents
Info
- Publication number
- DE87973C DE87973C DENDAT87973D DE87973DA DE87973C DE 87973 C DE87973 C DE 87973C DE NDAT87973 D DENDAT87973 D DE NDAT87973D DE 87973D A DE87973D A DE 87973DA DE 87973 C DE87973 C DE 87973C
- Authority
- DE
- Germany
- Prior art keywords
- sulfonic acid
- diazotized
- combined
- amidonaphthol
- phenol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 13
- 239000000975 dye Substances 0.000 claims description 11
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 210000002268 Wool Anatomy 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-Naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- -1 naphthylamine sulfonic acids Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/36—Trisazo dyes of the type
- C09B35/362—D is benzene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMTPATENT OFFICE
Das Verfahren bezweckt die Herstellung gewisser durch die Gegenwart der Ci1 ß3- bezw. Ci1 ß4 - Naphtylaminsulfosäure einerseits und ρ - Phenylendiamin andererseits charakterisirter Trisazofarbstoffe, welche durch die Fähigkeit ausgezeichnet sind, Wolle und Baumwolle gleichmä'fsig in einem Bade anzufärben und eine hervorragende Lichtechtheit besitzen. Das Herstellungsverfahren besteht darin, dafs man die Azokörper vom TypusThe purpose of the process is to produce certain by the presence of Ci 1 ß 3 - respectively. Ci 1 ß 4 - naphthylamine sulfonic acid on the one hand and ρ - phenylenediamine on the other hand characterized trisazo dyes, which are distinguished by the ability to dye wool and cotton evenly in one bath and have excellent lightfastness. The manufacturing process consists in using the azo bodies of the type
(O1)N=N-(O 1 ) N = N-
oderor
(ß3 (ß 3
(a,) N = N (a,) N = N
:4) S O3 H : 4 ) S O 3 H
C6 H1 -N H.2(p) R C 6 H 1 -N H. 2 (p) R
(wo R den Rest eines Phenols bedeutet) diazotirt und mit y-Amidonaphtolsulfosä'ure combinirt. Körper von obiger Zusammensetzung werden erhalten, indem Acet-p-phenyiendiamin mit Ci1 ß3- oder Ci1 ß4 - Naphtylaminsulfosäure combinirt, dann weiter diazotirt, mit einem Phenol (R) gemäfs dem Patent Nr. 83572 bezw. Nr. 84460 verbunden und hierauf die Acetylgruppe verseift wird. (Statt des Acet-p-phenylendiamins kann auch das p-Nitranilin verwendet werden. An Stelle der Verseifung tritt dann eine Reduction mit Schwefelalkalien.)(where R denotes the remainder of a phenol) diazotized and combined with γ-amidonaphthol sulfonic acid. Bodies of the above composition are obtained by combining acet-p-phenylenediamine with Ci 1 ß 3 - or Ci 1 ß 4 - naphthylamine sulfonic acid, then further diazotizing, with a phenol (R) according to patent no. No. 84460 connected and then the acetyl group is saponified. (Instead of acet-p-phenylenediamine, p-nitroaniline can also be used. Instead of saponification, a reduction with alkaline sulfur takes place.)
Von den in der englischen Patentschrift Nr. 16484/87 beschriebenen Combinationen unterscheiden sich die neuen. Farbstoffe zunächst durch die Gegenwart, des sulfirten Naphtylamins in Mittelstellung, die denselben die Affinität zur Wollfaser und damit den Charakter sogenannter Halbwollfarbstoffe verleiht. Aufserdem aber ist im vorliegenden Falle die Benutzung der y-Amidonaphtolsulfosäure als Endcompenente von ausschlaggebendem Einflufs 1 auf die Lichtechtheit und die chemischen Eigenschaften (wie z. B. Diazotirbarkeit der Producte).Of the combinations described in English patent specification No. 16484/87 differ the new. Dyes first through the presence, the sulphured Naphthylamine in the middle position, which has the same affinity for the wool fiber and thus gives the character of so-called semi-wool dyes. In addition, however, is in the present Fall using y-amidonaphthol sulfonic acid as end components of decisive influence 1 on the light fastness and the chemical properties (such as the diazotizability of the products).
Die Farbstoffe des französischen Patentes Nr. 219424 enthalten zwar auch, wie die hier beschriebenen, die Cl eve'sehen Naphtylaminsulfosäuren in Mittelstellung, zeigen jedoch keine Affinität zur Baumwollfaser und sind als Disazofarbstoffe in ihrem ganzen Bau von den neuen Trisazocombinationen verschieden.The dyes of French patent no. 219424 also contain, like the one here described, the Cl eve see naphthylamine sulfonic acids in the middle position, but show no affinity for cotton fibers and are as Disazo dyes differ in their whole structure from the new trisazo combinations.
ι 5 kg Acet-p-phenylendiamin werden diazotirt und mit 25 kg Ci1 ß3-Naphtylaminsulfosäure combinirt, nach vollendeter Farbstoff bildung wird angesäuert und mit 7 kg Nitrit diazotirt. Die rothbraun gefärbte Diazoazoverbindung wird in eine Lösung von 25 kg Ci1 α,-Naphtolsulfosäure eingetragen. Nach vollendeter Reaction wird ein Ueberschufs von Natronhydrat hinzugegeben und einige Zeit zum Kochen erhitzt. Man erhält hierbei eine Lösung der ρ -Amidobenzol- azo -Ci1- Naphtylamin - ß3- sulfosäure-azo-cij -Naphtol-c.g-sulfosäure. Wird nun die erkaltete Lösung angesäuert und mit 7 kg Nitrit versetzt, so wird eine Diazoverbin-5 kg of acet-p-phenylenediamine are diazotized and combined with 25 kg of Ci 1 ß 3 -naphthylamine sulfonic acid, after the formation of the dye is acidified and diazotized with 7 kg of nitrite. The red-brown colored diazoazo compound is introduced into a solution of 25 kg of Ci 1 α, -naphthol sulfonic acid. When the reaction is complete, an excess of sodium hydrate is added and the mixture is heated to the boil for a while. A solution of ρ-amidobenzene-azo- Ci 1 -naphthylamine-ß 3 -sulfonic acid-azo-cij -naphthol-cg-sulfonic acid is obtained. If the cooled solution is now acidified and mixed with 7 kg of nitrite, a diazo compound is
dung jenes Körpers gebildet. Die Bildung ist nach ca. einer Stunde beendet. Man trägt dann den Diazokörper in die alkalische Lösung von 27 kg P1 a4-Amidonaphtol-ß3-sulfosäure (7) ein. Der Farbstoff bildet sich sofort. Er wird durch Kochsalz vollständig abgeschieden. Er färbt ungeheizte Baumwolle blauschwarz.formation of that body. The formation is over after about an hour. The diazo body is then introduced into the alkaline solution of 27 kg of P 1 a 4 -amidonaphthol-β 3 -sulfonic acid (7). The dye forms immediately. It is completely separated out by table salt. It dyes unheated cotton blue-black.
In analoger Weise werden die folgenden Combinationen erhalten:The following combinations are obtained in an analogous manner:
ρ - Amidobenzol - azo - Naphtylaminsulfosäure (% ß3 oder Ct1 ß4) - azo-:ρ - amidobenzene - azo - naphthylamine sulfonic acid (% ß 3 or Ct 1 ß 4 ) - azo-:
Phenol phenol
Ct1 Ct2 - Naphtolsulfosäure Ct 1 Ct 2 - naphthol sulfonic acid
β - Naphtoldisulfosäure R β - naphthalene disulfonic acid R
ß1 a4 - Dioxynaphtalin - ß3 - sulfosäure .
K1 Ct4- Dioxynaphtalin - a2 - sulfosäure . ß 1 a 4 - dioxynaphthalene - ß 3 - sulfonic acid.
K 1 Ct 4 - dioxynaphthalene - a 2 - sulfonic acid.
diazotirt unddiazotized and
combinirt
mit ^-Amidonaphtolsulfosäure färbt ungeheizte Baumwollecombined
unheated cotton is dyed with amidonaphthol sulfonic acid
schwarz
schwarzblaublack
black blue
graublau
grünschwarz grünschwarz.gray-blue
green-black green-black.
Claims (1)
SO .1.
SO
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE87973C true DE87973C (en) |
Family
ID=359902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT87973D Active DE87973C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE87973C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004046252A1 (en) | 2002-11-15 | 2004-06-03 | Avecia Inkjet Limited | Trisazo dyes for inks for ink jet printing |
-
0
- DE DENDAT87973D patent/DE87973C/de active Active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004046252A1 (en) | 2002-11-15 | 2004-06-03 | Avecia Inkjet Limited | Trisazo dyes for inks for ink jet printing |
| US7530685B2 (en) | 2002-11-15 | 2009-05-12 | Fujifilm Imaging Colorants Limited | Trisazo dyes for inks for ink jet printing |
| CN1738868B (en) * | 2002-11-15 | 2010-07-14 | 富士胶片映像着色有限公司 | Trisazo dyes for inks for ink jet printing |
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